Literature DB >> 20297836

N,N'-diamidoketenimines via coupling of isocyanides to an N-heterocyclic carbene.

Todd W Hudnall1, Eric J Moorhead, Dmitry G Gusev, Christopher W Bielawski.   

Abstract

Treatment of an N-heterocyclic carbene that features two amide groups N-bound to the carbene nucleus with various organic isocyanides afforded a new class of ketenimines in yields of up to 96% (isolated). DFT analyses revealed that the carbene exhibits a unique, low-lying LUMO, which may explain the atypical reactivity observed.

Entities:  

Year:  2010        PMID： 20297836     DOI： 10.1021/jo100427g

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  7 in total

1.  Diamidocarbenes as versatile and reversible [2 + 1] cycloaddition reagents.

Authors:  Jonathan P Moerdyk; Christopher W Bielawski
Journal:  Nat Chem       Date:  2012-02-12       Impact factor: 24.427

2.  A Ruthenium Catalyst for Olefin Metathesis Featuring an Anti-Bredt N-Heterocyclic Carbene Ligand.

Authors:  David Martin; Vanessa M Marx; Robert H Grubbs; Guy Bertrand
Journal:  Adv Synth Catal       Date:  2016-02-09       Impact factor: 5.837

3.  Intercepting the Breslow intermediate via Claisen rearrangement: synthesis of complex tertiary alcohols without organometallic reagents.

Authors:  Sefat Alwarsh; Kolawole Ayinuola; Silvana S Dormi; Matthias C McIntosh
Journal:  Org Lett       Date:  2012-12-05       Impact factor: 6.005

4.  A cyclic diaminocarbene with a pyramidalized nitrogen atom: a stable N-heterocyclic carbene with enhanced electrophilicity.

Authors:  David Martin; Nicolas Lassauque; Bruno Donnadieu; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-08       Impact factor: 15.336

5.  A theoretical study on the hydrogen adducts of diamidocarbenes and diaminocarbenes.

Authors:  Chin Hung Lai
Journal:  J Mol Model       Date:  2013-11-19       Impact factor: 1.810

6.  Organocatalytic activation of isocyanides: N-heterocyclic carbene-catalyzed enaminone synthesis from ketones.

Authors:  Jungwon Kim; Soon Hyeok Hong
Journal:  Chem Sci       Date:  2016-12-20       Impact factor: 9.825

7.  Copper diamidocarbene complexes: characterization of monomeric to tetrameric species.

Authors:  Lee R Collins; John P Lowe; Mary F Mahon; Rebecca C Poulten; Michael K Whittlesey
Journal:  Inorg Chem       Date:  2014-02-11       Impact factor: 5.165
  7 in total

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